York was mentioned in James Madison Sr.’s records beginning in 1768, and continuing through the 1780s. He was issued a pair of size 6 shoes on November 2, 1787.
Benjamin McDaniel, who often worked as a courier, traveled over 50 miles to Dr. Henkal’s in New Market in June 1843, carrying a pass signed by Dolley Madison.
Milly, sometimes called “Granny Milly,” was 104 years old when she met General Lafayette at Montpelier in 1825. She lived in a cabin with her daughter and 70-year-old granddaughter.
Clarissa’s name appears on James Madison Sr.’s tax records in the 1780s. She may be the same woman as Clarisea, who was listed on Ambrose Madison’s 1732 inventory.
Gabriel was in his 50s when Dolley Madison gave him to her son John Payne Todd in 1844. Todd tried to free Gabriel in his will, but due to estate debts, this likely never happened.
Daphne was enslaved by James Madison Sr. in the 1780s. Her son Shadrach and daughter Anna were inherited by Madison Sr.’s son-in-law, Isaac Hite, in 1801.
Aleck drove James Madison’s wagon to Fredericksburg and Richmond in the 1820s and 30s, delivering tobacco and wheat to merchants, and returning with goods for the Madisons.
Silvey was sold with her children Fanny, Abraham, Frank, Elizabeth, and William to Montpelier’s new owner, Henry Moncure, for $1000. Silvey died in childbirth on April 18, 1847.